Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes,Journal of the American Chemical Society

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Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2021-08-26 , DOI: 10.1021/jacs.1c07851
Jian Chen ₁ , Shaolin Zhu ₁

Affiliation

A nickel-catalyzed, multicomponent regio- and enantioselective coupling via sequential hydroformylation and carbonylation from readily available starting materials has been developed. This modular multicomponent hydrofunctionalization strategy enables the straightforward reductive hydrocarbonylation of a broad range of unactivated alkenes to produce a wide variety of unsymmetrical dialkyl ketones bearing a functionalized α-stereocenter, including enantioenriched chiral α-aryl ketones and α-amino ketones. It uses chiral bisoxazoline as a ligand, silane as a reductant, chloroformate as a safe CO source, and a racemic secondary benzyl chloride or an N-hydroxyphthalimide (NHP) ester of a protected α-amino acid as the alkylation reagent. The benign nature of this process renders this method suitable for late-stage functionalization of complex molecules.

中文翻译：

镍催化多组分偶联：通过烯烃的还原烃基化合成 α-手性酮

已经开发出一种镍催化、多组分区域选择性和对映选择性偶联，通过顺序加氢甲酰化和羰基化从容易获得的起始材料中进行。这种模块化的多组分加氢官能化策略能够对各种未活化的烯烃进行直接的还原烃基化，以产生各种带有功能化 α-立体中心的不对称二烷基酮，包括对映体富集的手性 α-芳基酮和 α-氨基酮。它使用手性双恶唑啉作为配体，硅烷作为还原剂，氯甲酸酯作为安全的 CO 源，外消旋仲苄基氯或N受保护的 α-氨基酸的 -羟基邻苯二甲酰亚胺 (NHP) 酯作为烷基化试剂。该过程的良性性质使该方法适用于复杂分子的后期功能化。

更新日期：2021-09-08

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